5H-pyrrolo[3,2-d]pyrimidine

Base Information

• Chemical Name: 5H-pyrrolo[3,2-d]pyrimidine
• CAS No.: 272-50-4
• Molecular Formula: C₆H₅N₃
• Molecular Weight: 119.126
• Hs Code.: 2933990090
• European Community (EC) Number: 870-311-1
• DSSTox Substance ID: DTXSID401346584
• Nikkaji Number: J1.424.751C
• Mol file: 272-50-4.mol

Synonyms:pyrrolopyrimidine

Chemical Property of 5H-pyrrolo[3,2-d]pyrimidine

Chemical Property:

• Vapor Pressure: 0.00409mmHg at 25°C
• Melting Point: 175 °C (decomp)
• Refractive Index: 1.715
• Boiling Point: 288.3 °C at 760 mmHg
• PKA: 13.16±0.10(Predicted)
• Flash Point: 141.8 °C
• PSA: 41.57000
• Density: 1.348 g/cm³
• LogP: 0.95790
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 119.048347172
• Heavy Atom Count: 9
• Complexity: 105

Purity/Quality:

98%,99%, ^*data from raw suppliers

5H-Pyrrolo[3,2-d]pyrimidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CNC2=CN=CN=C21

Technology Process of 5H-pyrrolo[3,2-d]pyrimidine

There total 1 articles about 5H-pyrrolo[3,2-d]pyrimidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 61.0%

2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine (63200-54-4) → 2-chloro-5H-pyrrolo[3,2-d]pyrimidine? (1119280-66-8) + 5H-pyrrolo[3,2-d]pyrimidine (272-50-4)

Guidance literature:

With hydrogen; sodium hydrogencarbonate; palladium 10% on activated carbon; In ethanol; at 20 ℃; for 3h;

Reference yield:

5H-pyrrolo[3,2-d]pyrimidine (272-50-4) → 3-phenyl-4-(5H-pyrrolo[3,2-d]pyrimidin-7-yl)-1H-pyrrole-2,5-dione

Guidance literature:

Multi-step reaction with 2 steps

1.1: aluminum (III) chloride / dichloromethane / 6.5 h / 20 °C

2.1: potassium tert-butylate / tetrahydrofuran / 6 h / 20 °C / Cooling with ice; Inert atmosphere

2.2: 1 h / 20 °C

With aluminum (III) chloride; potassium tert-butylate; In tetrahydrofuran; dichloromethane;

Reference yield:

5H-pyrrolo[3,2-d]pyrimidine (272-50-4) → 2-(7-(1-((2-cyano-4-methyl-1H-indol-5-yl)methyl)piperidin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-5-yl)-5-fluoro-N-isopropyl-N-methylbenzamide

Guidance literature:

Multi-step reaction with 6 steps

1.1: potassium hydroxide / ethylene glycol / 18 h / 95 °C

2.1: palladium(II) hydroxide; hydrogen / methanol; tetrahydrofuran / 120 h / 45 °C / 2585.81 Torr

3.1: caesium carbonate / N,N-dimethyl-formamide / 18 h / 100 °C

4.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h / 20 °C

5.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 2 h / 0 - 20 °C

6.1: acetic acid / methanol / 0.5 h / 6 - 20 °C

6.2: 4 h / 55 °C

With hydrogenchloride; hydrogen; palladium(II) hydroxide; caesium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; potassium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; ethylene glycol; N,N-dimethyl-formamide;

upstream raw materials:

2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine

Refernces